3beta,8alpha-dihydroxyguaia-4(15),10(14)-dien-1alpha,5alpha,6beta,11betaH-12,6-olide 8-O-[2’(S)-3-hydroxy-2-methylpropionate] - Compound Card

3beta,8alpha-dihydroxyguaia-4(15),10(14)-dien-1alpha,5alpha,6beta,11betaH-12,6-olide 8-O-[2’(S)-3-hydroxy-2-methylpropionate]

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3beta,8alpha-dihydroxyguaia-4(15),10(14)-dien-1alpha,5alpha,6beta,11betaH-12,6-olide 8-O-[2’(S)-3-hydroxy-2-methylpropionate]

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles OC[C@@H](C(=O)O[C@H]1CC(=C)[C@H]2[C@@H]([C@@H]3[C@@H]1[C@H](C)C(=O)O3)C(=C)[C@H](C2)O)C
InChI InChI=1S/C19H26O6/c1-8-5-14(24-18(22)9(2)7-20)16-11(4)19(23)25-17(16)15-10(3)13(21)6-12(8)15/h9,11-17,20-21H,1,3,5-7H2,2,4H3/t9-,11-,12-,13-,14-,15-,16+,17+/m0/s1
InChIKey PMEAIKAPEVRFCE-YJGFUPBESA-N
Formula C19H26O6
HBA 6
HBD 2
MW 350.41
Rotatable Bonds 3
TPSA 93.06
LogP 1.22
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 25
Formal Charge 0
Fraction CSP3 0.68
Exact Mass 350.17
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Cheirolophus mauritanicus Asteraceae Plantae 64998

Showing of synonyms

  • Marco JA, Sanz-Cervera JF, et al. (1994). Sesquiterpene lactones, lignans and aromatic esters ftrom Cheirolophus species. Phytochemistry,1994,37(4),1101-1107. [View]
Pubchem: 101675258

No compound-protein relationship available.

Structure

SMILES: C=C1CCC2C(=C)CCC(C3C12)CC(=O)O3

Level: 0

Mol. Weight: 350.41 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.54
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.7
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.3

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.48
Plasma Protein Binding
53.89
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
7.82
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.49
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.19
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
5.01
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-4.73
Rat (Acute)
4.18
Rat (Chronic Oral)
2.04
Fathead Minnow
3.92
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
396.66
Hydration Free Energy
-8.22
Log(D) at pH=7.4
0.76
Log(P)
0.51
Log S
-2.45
Log(Vapor Pressure)
-7.98
Melting Point
156.94
pKa Acid
8.14
pKa Basic
5.09
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.9143
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.9143
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8530
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8530
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7483
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7483
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7354
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7354
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7287
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7287
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7255
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7255
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7236
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7236
Predicted acetyltransferase Q97ML2 Q97ML2_CLOAB Clostridium acetobutylicum 3 0.7196
Predicted acetyltransferase Q97ML2 Q97ML2_CLOAB Clostridium acetobutylicum 3 0.7196
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7024
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7024

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